HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Isle of Wight

$59+ Cheap flights from Portland, ME (PWM) to Isle of Wight, VA

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — RIC
oct. 16 — oct. 231
jue. 10/16
jue. 10/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Isle of Wight with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheapflights Tip: The best prices from Portland to Isle of Wight are usually found in May or August, booked 30 days in advance, depart on a Monday or Wednesday and return on a Tuesday

Cheap flight deals from Portland to Isle of Wight

Keep the following information in mind while searching for Portland to Isle of Wight flight deals. Data was last updated septiembre 16, 2025.

Round-trip from

$206
(Kiwi.com)

One-way from

$59
(Breeze Airways)

Popular in

February

Cheapest in

May

Average price

$305
From Portland to Isle of Wight
Search Deals
One-way flight from Portland to Isle of Wight
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($32 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

Find flight deals from Portland to Isle of Wight

Cheapest flights from Portland to Isle of Wight
Explore the most affordable flight options available from Portland to Isle of Wight. Find the lowest fares from popular airlines and budget airlines, with prices last updated on septiembre 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 10/17:37 pmPWM - ORF
Nonstop1h 46mMultiple Airlines
dom. 10/55:38 pmORF - PWM
1 stop15h 28mMultiple Airlines
Deal found 9/16$206
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/55:00 pmPWM - ORF
1 stop5h 23mDelta
mar. 11/116:59 pmORF - PWM
1 stop4h 20mDelta
Deal found 9/15$237
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/56:00 amPWM - ORF
1 stop4h 49mUnited Airlines
sáb. 11/86:35 amORF - PWM
1 stop7h 37mUnited Airlines
Deal found 9/14$247
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 11/155:40 amPWM - ORF
2 stops10h 40mSouthwest
mié. 11/198:30 amORF - PWM
1 stop3h 40mSouthwest
Deal found 9/15$252
This Delta deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/306:35 amPWM - ORF
1 stop4h 57mDelta
sáb. 10/42:00 pmORF - PWM
1 stop8h 00mDelta
Deal found 9/15$257
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/45:30 amPWM - ORF
2 stops11h 15mSouthwest
sáb. 11/86:10 amORF - PWM
1 stop5h 55mSouthwest
Deal found 9/14$283
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 11/53:30 pmPWM - ORF
1 stop6h 30mSouthwest
mar. 11/1110:05 amORF - PWM
2 stops12h 10mSouthwest
Deal found 9/15$288
This American Airlines deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/75:43 amPWM - ORF
1 stop3h 37mAmerican Airlines
mar. 11/112:35 pmORF - PWM
1 stop7h 00mAmerican Airlines
Deal found 9/16$302
This United Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/105:41 pmPWM - ORF
1 stop5h 51mUnited Airlines
mar. 10/147:59 pmORF - PWM
1 stop4h 00mUnited Airlines
Deal found 9/14$304
This Southwest deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/245:25 pmPWM - ORF
1 stop6h 10mSouthwest
vie. 11/288:15 pmORF - PWM
1 stop4h 05mSouthwest
Deal found 9/14$312
This Kiwi.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 9/301:18 pmPWM - ORF
3 stops51h 25mMultiple Airlines
mié. 10/85:15 pmORF - PWM
Nonstop1h 42mMultiple Airlines
Deal found 9/15$316

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Isle of Wight that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septiembre 16, 2025.
Use the filters below to find and compare flights from Portland to Isle of Wight that are best for you.

Fly from

Portland

Fly to

Isle of Wight

Route

Depart

Return

Price

PortlandNorfolk

PWM - ORF

PWMORF

Portland

mar. 2/24

6:00 am-10:22 am

1 stop4h 22m

Norfolk

mié. 2/25

7:00 am-1:51 pm

1 stop6h 51m

$237

PortlandNorfolk

PWM - ORF

PWMORF

Portland

mar. 2/24

6:00 am-10:22 am

1 stop4h 22m

Norfolk

mar. 2/24

5:00 pm-11:05 pm

1 stop6h 05m

$237

PortlandNorfolk

PWM - ORF

PWMORF

Portland

mié. 11/5

6:00 am-10:49 am

1 stop4h 49m

Norfolk

sáb. 11/8

6:35 am-2:12 pm

1 stop7h 37m

$247

PortlandNorfolk

PWM - ORF

PWMORF

Portland

mar. 11/4

6:00 am-12:31 pm

1 stop6h 31m

Norfolk

sáb. 11/8

7:04 am-1:58 pm

1 stop6h 54m

$247

PortlandNorfolk

PWM - ORF

PWMORF

Portland

sáb. 11/15

12:48 pm-5:39 pm

1 stop4h 51m

Norfolk

mié. 11/19

3:10 pm-10:19 pm

1 stop7h 09m

$247

PortlandNorfolk

PWM - ORF

PWMORF

Portland

mié. 11/5

6:50 am-11:29 am

1 stop4h 39m

Norfolk

sáb. 11/8

7:04 am-1:58 pm

1 stop6h 54m

$247

PortlandNorfolk

PWM - ORF

PWMORF

Portland

sáb. 10/25

6:30 am-11:23 am

1 stop4h 53m

Norfolk

mar. 10/28

5:24 am-12:22 pm

1 stop6h 58m

$247

PortlandNorfolk

PWM - ORF

PWMORF

Portland

mar. 9/30

6:35 am-11:32 am

1 stop4h 57m

Norfolk

mié. 10/8

5:29 pm-12:05 am

1 stop6h 36m

$247

PortlandNorfolk

PWM - ORF

PWMORF

Portland

sáb. 11/15

5:40 am-4:20 pm

2 stops10h 40m

Norfolk

mié. 11/19

8:30 am-12:10 pm

1 stop3h 40m

$252

PortlandNorfolk

PWM - ORF

PWMORF

Portland

mié. 11/5

5:30 am-3:30 pm

2 stops10h 00m

Norfolk

sáb. 11/8

11:30 am-2:40 pm

1 stop3h 10m

$283

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 22 results
1
2
3

Best time to book a flight from Portland to Isle of Wight

Have a flexible travel schedule? Discover the best time to fly to Isle of Wight from Portland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Portland to Isle of Wight

How far ahead should I book a flight from Portland, Maine to Isle of Wight?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Isle of Wight. Price data was last updated on September 12, 2025.

The price you pay for your flight from Portland, Maine to Isle of Wight may vary depending on when you book. For the best chance of a lower fare, look to book 30 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

What is the cheapest month to book a flight from Portland, Maine to Isle of Wight?

Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Isle of Wight (average of $281). Flying from Portland, Maine to Isle of Wight in March is currently the most expensive (average of $351). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from PWM to I1W?

Find hourly flight availability from Portland to Isle of Wight. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 16, 2025.

When flying from Portland, Maine to Isle of Wight, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

What is the cheapest day to fly from Portland, Maine to Isle of Wight?

Use this chart to determine the cheapest time to fly round-trip from Portland to Isle of Wight. Price data was last updated on December 16, 2024.

Travelers seeking maximum savings on their Portland, Maine to Isle of Wight flight should consider departing on Monday evenings when fares are most often at their lowest. Sunday at noon flights should be avoided if possible as fares are typically the most expensive at this time.

Reviews of airlines servicing Isle of Wight

Get insights into the airlines that provide service to Isle of Wight. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Isle of Wight. Reviews last updated septiembre 16, 2025.
Peruse reviews from past customers who have flown with Southwest, Breeze Airways, and Delta from Portland to Isle of Wight to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Breeze Airways
8.0
Very good
205 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,957 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,924 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,242 reviews

Entertainment

7.5

Crew

8.6

Boarding

8.1

Food

7.0

Comfort

8.0

Overall

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Related info for your journey

Find useful and relevant information for your journey from Portland to Isle of Wight. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Portland to Isle of Wight?

    For a flight from Portland to Isle of Wight, you will be flying from Portland. Portland (PWM) is just 2.9 mi from the center of the city. Portland is the only Portland airport and it handles 0 outbound flights to Isle of Wight per day. 5 airlines have flights to Isle of Wight from Portland on a regular basis.

  • How long is the flight from Portland, Maine to Isle of Wight?

    A quick flight from Portland, Maine to Isle of Wight can take about 4h 22m. Delta provides one of the quickest options available for as low as $237. Airlines will cover a distance of 560 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Portland, Maine to Isle of Wight one-way?

    One-way options have recently been found by users for as low as $59 on Breeze Airways. Other airlines that offer cheap prices include United Airlines from $129 and American Airlines from $129 one-way.

  • Can I find deals for flights from Portland to Isle of Wight that include hotel bookings?

    Yes. In addition to deals on Portland to Isle of Wight flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Isle of Wight?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Isle of Wight.

  • Can I find deals for business class flights from Portland to Isle of Wight?

    Yes. Cheapflights offers flight deals from Portland to Isle of Wight by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Portland, Maine to Isle of Wight?

    Currently, January is the cheapest month in which you can book a flight from Portland, Maine to Isle of Wight (average of $281). Flying from Portland, Maine to Isle of Wight in March is currently the most expensive (average of $351). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Isle of Wight

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Reagan-National flights
Boston to Raleigh flights
Boston to Dulles Intl flights
Boston to Richmond flights
Portland to Dulles Intl flights
Portland to Reagan-National flights
Boston to Norfolk flights
Boston to Greensboro flights
Boston to Charlottesville flights
Portland to Richmond flights
Portland to Raleigh flights
Boston to Roanoke flights
Portland to Norfolk flights
Bangor to Dulles Intl flights
Bangor to Richmond flights
Bangor to Reagan-National flights
Portland to Charlottesville flights
Bangor to Raleigh flights
Bangor to Norfolk flights
Boston to Newport News flights
Boston to Lynchburg flights
Augusta to Raleigh flights
Boston to Salisbury flights
Portland to Greensboro flights
Portland to Roanoke flights
Rockland to Raleigh flights
Boston to Blountville flights
Portland to Newport News flights
Augusta to Reagan-National flights
Bangor to Charlottesville flights
Boston to Staunton flights
Bar Harbor to Reagan-National flights
Bangor to Blountville flights
Portland to Blountville flights
Boston to Lewisburg flights
Augusta to Dulles Intl flights
Portland to Staunton flights
Rockland to Dulles Intl flights

Top 5 airlines flying from Portland to Isle of Wight

Discover the top 5 airlines that operate flights from Portland to Isle of Wight. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated septiembre 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
Breeze AirwaysCheapest$67Average$159FlexibilityNo cancel feeOn-timeN/A
DeltaCheapest$118Average$301FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$194Average$361FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$218Average$348FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$248Average$374FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.